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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 23
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Original Articles

Synthesis of Some Novel α-Cyanoketene-N,S-acetals Derived from Secondary Aliphatic Amines and Their Use in Pyrazole Synthesis

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Pages 3203-3216 | Received 12 Jan 2013, Published online: 04 Sep 2013

REFERENCES

  • Yokoyama , M. ; Togo , H. ; Kondo , S. Synthesis of hetero cycles from ketene dithioacetals . Sulfur Rep. 1990 , 10 ( 1 ), 23 – 47 .
  • Tominaga , Y. ; Kohra , S. ; Honkawa , H. ; Hosoni , A. Synthesis of pyrimidine derivatives and their related compounds using ketene dithioacetals . Tetrahedron 1986 , 42 ( 12 ), 3029 – 3096 .
  • Dieter , R. K. α-Oxo ketene dithioacetals and related compounds: Versatile three-carbon synthons . Tetrahedron 1986 , 42 ( 12 ), 3029 – 3096 .
  • Misra , N. C. ; Panda , K. ; Ila , H. ; Junjappa , H. An efficient highly region selective synthesis of 2,3,4-trisubstitutedpyrroles by cycloaddition of polarized ketene-S,S- and N,S-acetals with activated methylene isocyanides . J. Org. Chem. 2007 , 72 , 1246 – 1251 .
  • Khalil , A. M. ; Berghot , M. A. ; Gouda , M. A. Synthesis and antibacterial activity of some new hetero cycles incorporating phthalazine . Eur. J. Med. Chem. 2009 , 44 , 4448 – 4454 .
  • Patel , H. V. ; Fernandes , P. S. ; Vyas , K. A. A novel synthesis of a few substituted s-triazolo[3,4-b][1,3,4]thiadiazoles and evaluation of their antibacterial activity . Indian J. Chem. 1990 , 29B , 135 .
  • Farhat , M. F. ; El-Saghier , A. M. M. ; Makhlouf , M. A ; Kreddan , K. M. Elmezoughi , A. B. Ketene N,S-acetals in heterocyclic synthesis, part 1: Synthesis of N-phenyl-2-ylidene and 2,5-diylidene-4-thiazolidinone derivatives . J. Sulfur Chem. 2007 , 28 ( 6 ), 563 – 572 .
  • El-Shafei , A. K. ; Abdel-Ghany , H. A. ; Sultan , A. ; El-Saghier , A. M. M. Synthesis of thieno (2,3-b) thiophene and related structures . Phosphorus, Sulfur Silicon Relat. Elem. 1992 , 73 , 15 – 25 .
  • Farhat , M. F. ; Makhlouf , M. A. ; El-Saghier , A. M. M. ; Mezoughi , A. B. A. ; Awhida , S. M. ; El-mehdi , A. A. M. Utilization of 2-ylidene-thiazolidinones in the synthesis of heterocyclic compounds, part I: Synthesis of pyrazoles . Arab. J. Chem. 2011 , 4 , 307 – 311 .
  • Chen , H. S. ; Li , Z. M. Synthesis of some heteroaryl pyrazole derivatives and their biological activities . Chin. J. Chem. 2000 , 18 , 596 .
  • Elgemeie , G. H. ; Elghandour , A. H. ; AbdElaziz , G. W. Novel synthesis of heterocyclic ketene-N,N-, N,O-, and -N,S-acetals using cyanoketenedithioacetals . Synth. Commun. 2003 , 33 ( 10 ), 1659 – 1664 .
  • Morimoto , K. M. ; Makino , K. ; Yamamoto , S. ; Sakato , G. Synthesis of fluoromethyl, difluoromethyl, and trifluoromethyl analogues of pyrazosulfuron-ethyl as herbicides . J. Heterocycl. Chem. 1990 , 27 , 807 .
  • Huang , R. Q. ; Song , J. ; Feng , L. Synthesis and bioactivity of 1,3,5-substituted pyrazol-4-ylmethyl cyclopropanecarboxylates . Chem. J. Chin. Univ. 1996 , 17 , 1089 .
  • Elgemeie , G. H. ; Elghandour , A. H. ; Elzanate , A. M. ; Ahmed , S. A. Synthesis of some novel α-cyanoketene S,S-acetals and their use in heterocyclic synthesis. J. Chem. Soc. Perkin Trans. 1 1997 , 3285 – 3290 .
  • Elgemeie , G. H. ; Elghandour , A. H. ; Elaziz , G. W. A. Novel cyanoketene N,S-acetals and pyrazolederivatives using potassium 2-cyanoethylene-1-thiolates . Synth. Commun. 2007 , 37 , 2827 – 2834 .
  • Gouda , M. A. ; Berghot , M. A. ; Shoeib , A. I. ; Khalil , A. M. Synthesis and antimicrobial activity of new anthraquinone derivatives incorporating pyrazole moiety . Eur. J. Med. Chem. 2010 , 45 , 1843 – 1848 .
  • Zaharan , M. A. ; El-Sharief , A. M. S. , El-Gaby , M. S. A. ; Ammar , Y. A. ; El-Said , U. H. Synthesis of antimicrobial pyrazolo[1,5-a]pyrimidines via the reaction of ketene dithioacetals and 5-aminopyrazoles. Farmaco. 2001, 56, 277–283.
  • Gouda , M. A. ; Berghot Ghada , E. A. ; Khalil , A. M. Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4, 5, 6, 7-tetrahydrobenzothiophene moiety . Eur. J. Med. Chem. 2010 , 45 , 1338 – 1345 .
  • Elgemeie , G. H. ; Elghandour , A. H. ; AbdElaziz , G. W. A new preparative route to 2-cyanoketene-S,N-acetals and pyrazole derivatives . Synth. Commun. 2004 , 34 ( 18 ), 3281 – 3291 .
  • Yoshikata , K. ; Seigo , K. Reactions of ketenethioacetals, I: Its reaction with some amines and active methylene compounds. J. Pharm. Soc. Jpn. 1965 , 85 ( 5 ), 387 – 390 .
  • Allen , F. H. ; Kennard , O. ; Watson , D. G. ; Brammer , L. ; Orpen , A. G. ; Taylor , R. Table of bond lengths determined by x-ray and neutron diffraction, part 1: Bond lengths in organic compounds . J. Chem. Soc. Perkin Trans. 2 1987 , S1–S19.
  • Sommen , G. ; Comel , A. ; Kirsch , G. Preparation of thieno[2,3-b]pyrroles starting from ketene-N,S-acetals . Tetrahedron 2003 , 59 , 1557 .

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